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112577

Sigma-Aldrich

L-(−)-Malic acid

97%, optical purity ee: 99% (GLC)

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Synonym(s):
(S)-(−)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid
Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
Molecular Weight:
134.09
Beilstein:
1723541
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

powder

optical activity

[α]20/D −27°, c = 5.5 in pyridine

optical purity

ee: 99% (GLC)

mp

101-103 °C (lit.)

SMILES string

O[C@@H](CC(O)=O)C(O)=O

InChI

1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

InChI key

BJEPYKJPYRNKOW-REOHCLBHSA-N

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This Item
M6413M739709172
L-(−)-Malic acid 97%, optical purity ee: 99% (GLC)

Sigma-Aldrich

112577

L-(−)-Malic acid

-
L-(−)-Malic acid BioXtra, ≥95%

Sigma-Aldrich

M6413

L-(−)-Malic acid

Premium Grade
L-(−)-Malic acid BioReagent, suitable for cell culture, suitable for insect cell culture

Sigma-Aldrich

M7397

L-(−)-Malic acid

-
L-(−)-Malic acid certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

09172

L-(−)-Malic acid

-
form

powder

form

powder

form

powder

form

-

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

optical activity

[α]20/D −27°, c = 5.5 in pyridine

optical activity

-

optical activity

-

optical activity

-

optical purity

ee: 99% (GLC)

optical purity

-

optical purity

-

optical purity

-

General description

L-(-)-Malic acid is an organic acid that is commonly found in wine. It plays an important role in wine microbiological stability.

Application

L-(-)-Malic acid is a selective α-amino protecting reagent for amino acid derivatives. It is also a versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 48, 5601-5601 (2007)
I Yoshpe-Besançon et al.
Biotechnology and applied biochemistry, 18 ( Pt 1), 93-102 (1993-08-01)
In previous papers we have reported that an aminopeptidase A (EC 3.4.11.7) purified from Staphylococcus chromogenes was able to catalyse the introduction of L-malic acid at the N-terminus of Tyr and Phe derivatives. We now show that this enzyme can
Bioorganic & Medicinal Chemistry Letters, 2, 1713-1713 (1992)
Zhigen Li et al.
Journal of synchrotron radiation, 27(Pt 1), 100-109 (2019-12-24)
Aluminium (Al) K- and L-edge X-ray absorption near-edge structure (XANES) has been used to examine Al speciation in minerals but it remains unclear whether it is suitable for in situ analyses of Al speciation within plants. The XANES analyses for
Kinetic determination of L (-) malic acid in wines using sequential injection analysis.
Segundo MA and Rangel AOSS.
Analytica Chimica Acta, 499(1), 99-106 (2003)

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